Attachment of carbonyl functionalities onto olefins via copper-promoted radical reaction of dichloromethylcyanides

Tetrahedron

Volumn 68, Issue 26, 2012, Pages 5290-5296

  Kamijo, Shin ^a   Yokosaka, Shinya ^a   Inoue, Masayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Carbonyl functionality; Copper catalysis; Olefin; Radical reaction

Indexed keywords

ALDEHYDE; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; COPPER CHLORIDE; CYANIDE; DICHLOROMALONONITRILE; DICHLOROMETHYLCYANIDE DERIVATIVE; ESTER; KETONE; TRICHLOROACETONITRILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; PRIORITY JOURNAL; RADICAL REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 84861685598     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.01.089     Document Type: Article

References (36)

1. M.F. Semmelhack B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 4 1991 Pergamon Oxford
2. P. Perlmutter Conjugated Addition Reactions in Organic Synthesis 1992 Pergamon Oxford
3. For a review of transition metal-catalyzed radical reactions in organic synthesis, see: J. Iqbal, B. Bhatia, and N.K. Nayyar Chem. Rev. 94 1994 519
4. B. Giese Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds 1986 Pergamon Oxford
5. Curran, D. P. In Ref. 1a, p 715.
6. S. Murai, and S. Tsutsumi J. Org. Chem. 31 1966 3000
7. M. Julia, G. Le Thuillier, and L. Saussine J. Organomet. Chem. 177 1979 211
8. R.G. Pews, and Z. Lysenko J. Org. Chem. 50 1985 5115
9. T.K. Hayes, R. Villani, and S.M. Weinreb J. Am. Chem. Soc. 110 1988 5533
10. M. Mori, Y. Kubo, and Y. Ban Heterocycles 31 1990 433
11. A.S. Dneprovskii, A.N. Kasatochkin, V.P. Boyarskii, A.A. Ermoshkin, and A.A. Yakovlev Russ. J. Org. Chem. 42 2006 1120
12. K. Thommes, M.A. Fernández-Zúmel, C. Buron, A. Godinat, R. Scopelliti, and K. Severin Eur. J. Org. Chem. 2011 249
13. L.M. Weinstock, S. Karady, F.E. Roberts, A.M. Hoinowski, G.S. Brenner, T.B.K. Lee, W.C. Lumma, and M. Sletzinger Tetrahedron Lett. 16 1975 3979
14. M. Mizuno, K. Kobayashi, H. Nakajima, M. Koya, and T. Inazu Synth. Commun. 32 2002 1665
15. D.P. Curran, and G. Thoma J. Am. Chem. Soc. 114 1992 4436
16. Y. Kita, K. Gotanda, K. Murata, M. Suemura, A. Sano, T. Yamaguchi, M. Oka, and M. Matsugi Org. Process Res. Dev. 2 1998 250
17. E.J. Corey, N.M. Weinshenker, T.K. Schaaf, and W. Huber J. Am. Chem. Soc. 91 1969 5675
18. D.A. Evans, W.L. Scott, and L.K. Truesdale Tetrahedron Lett. 13 1972 121
19. J.A. Kepler, F.I. Carroll, R.A. Garner, and M.E. Wall J. Org. Chem. 31 1966 105
20. D.O. Jang, D.J. Park, and J. Kim Tetrahedron Lett. 40 1999 5323
21. H.-P. Buchstaller, H.M. Ebert, and U. Anlauf Synth. Commun. 31 2001 1001
22. I. Vágó, and I. Greiner Tetrahedron Lett. 43 2002 6039
23. C.L. Stevens, and T.H. Coffield J. Am. Chem. Soc. 73 1951 103
24. L.-h. Zhang, G.S. Kauffman, J.A. Pesti, and J. Yin J. Org. Chem. 62 1997 6918
25. T. Hata Bull. Chem. Soc. Jpn. 37 1964 547
26. S. Förster, O. Tverskoy, and G. Helmchen Synlett 2008 2803
27. H. Nemoto, Y. Kubota, and Y. Yamamoto J. Org. Chem. 55 1990 4515
28. H. Nemoto, X. Li, R. Ma, I. Suzuki, and M. Shibuya Tetrahedron Lett. 44 2003 73
29. H. Nemoto, T. Kawamura, K. Kitasaki, K. Yatsuzuka, M. Kamiya, and Y. Yoshioka Synthesis 2009 1694
30. K. Ramsamy, R.K. Olsen, and T. Emery Synthesis 1982 42
31. A.K. Chatterjee, T.-L. Choi, D.P. Sanders, and R.H. Grubbs J. Am. Chem. Soc. 125 2003 11360
32. B.E. Maryanoff, and A.B. Reitz Chem. Rev. 89 1989 863
33. K.C. Nicolaou, M.W. Härter, J.L. Gunzner, and A. Nadin Liebigs Ann./Recueil 1997 1283
34. L. Palais, L. Babel, A. Quintard, S. Belot, and A. Alexakis Org. Lett. 12 2010 1988
35. L.J. Drummond, and A. Sutherland Tetrahedron 66 2010 5349
36. A.A. Poeylaut-Palena, S.A. Testero, and E.G. Mata J. Org. Chem. 73 2008 2024